Tired of Small Talk? Use These Questions to Generate Better Conversations

Questions to Promote Conversations
And Guidelines to Keep Conversations Productive



  • Who (living or dead) would you like to invite for dinner and why? What would you ask them?
  • What was your favorite toy as a child and why? Can you remember where you got it?
  • If you could wake up tomorrow with a new skill or ability, what would you choose? What would you do with that talent?
  • What three objects do you value most?
  • What was your favorite movie and why? What was it about the movie that you liked?
  • If you could possess one artistic talent, which would you choose and why? What would you do with that talent?
  • Which of your parents do you think you are most like and why?
  • If you could be an Olympic or professional athlete, what sport would you choose and why?
  • What skill, quality or talent are you most proud of and why?
  • What is the most courageous or hardest thing you have ever done? What happened?  What did you learn about yourself?
  • If you could witness an event in history, what would it be? What would you like to learn by being there?
  • If you had a magic wand and could use it once, what would you do with it? What is important about that for you?
  • What trip/holiday had a lasting impact on you?  If you went there again, would you do anything different?
  • What is more important to you:  free time, recognition, money or something else?
  • What is the proudest moment in your life?  Did it change you in any way?
  • When were you really scared?  How did you manage it and what happened? 


Continue to ask open questions or “say more about that” to encourage deeper conversations and to convey interest.  

Listen actively using techniques like mirroring and paraphrasing to communicate you are present, responsive and engaged.

Validate the person’s perspective and help them savor their ideas.

Label feelings to show connection and compassion.

Resist the urge to play Devil’s Advocate, relate it to yourself, go on a tangent, point out a problem or attempt to solve it (in that moment—you can always revisit an issue later).